NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.08
Volume:	264.59
LogP:	1.863
LogD:	1.169
LogS:	-3.258
# Rotatable Bonds:	1
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.757
Synthetic Accessibility Score:	3.798
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.92
MDCK Permeability:	7.343456218222855e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.428
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.707
30% Bioavailability (F30%):	0.828

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.273
Plasma Protein Binding (PPB):	71.62350463867188%
Volume Distribution (VD):	0.821
Pgp-substrate:	29.025686264038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.728
CYP1A2-substrate:	0.23
CYP2C19-inhibitor:	0.271
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.36
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.574
CYP2D6-substrate:	0.408
CYP3A4-inhibitor:	0.647
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	8.768
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.517
Skin Sensitization:	0.163
Carcinogencity:	0.434
Eye Corrosion:	0.004
Eye Irritation:	0.062
Respiratory Toxicity:	0.252

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC316535

Natural Product ID:	NPC316535
*Common Name:**	Microdiplodiasone
IUPAC Name:	(2R)-5,7-dihydroxy-2-methyl-2-[(2R)-5-oxooxolan-2-yl]-3H-chromen-4-one
Synonyms:	Microdiplodiasone
Standard InCHIKey:	KYUNATJAFQPBJE-BXUZGUMPSA-N
Standard InCHI:	InChI=1S/C14H14O6/c1-14(11-2-3-12(18)19-11)6-9(17)13-8(16)4-7(15)5-10(13)20-14/h4-5,11,15-16H,2-3,6H2,1H3/t11-,14-/m1/s1
SMILES:	O=C1CC[C@@H](O1)[C@@]1(C)CC(=O)c2c(O1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765410
PubChem CID:	52937071
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33247	microdiplodia sp.	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21244021]
NPO30809	Microdiplodia	Genus	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21244021]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	0.0	mm	PMID[474922]
NPT1465	Organism	Legionella pneumophila	Legionella pneumophila	MIC	=	1000.0	ug.mL-1	PMID[474922]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC316535 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	1344
0.2-0.3	3274
0.3-0.4	7674
0.4-0.5	10515
0.5-0.6	4645
0.6-0.7	5572
0.7-0.8	6358
0.8-0.85	2258
0.85-0.9	741
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9247	High Similarity	NPC180351
0.9225	High Similarity	NPC171870
0.9189	High Similarity	NPC301233
0.9172	High Similarity	NPC202494
0.9167	High Similarity	NPC297788
0.9155	High Similarity	NPC307287
0.9122	High Similarity	NPC256141
0.9116	High Similarity	NPC116822
0.9085	High Similarity	NPC37206
0.9054	High Similarity	NPC472580
0.9054	High Similarity	NPC472636
0.9048	High Similarity	NPC477941
0.9041	High Similarity	NPC47388
0.9041	High Similarity	NPC473133
0.9041	High Similarity	NPC470670
0.9041	High Similarity	NPC91902
0.9041	High Similarity	NPC85773
0.9034	High Similarity	NPC470857
0.9028	High Similarity	NPC130206
0.9	High Similarity	NPC108937
0.9	High Similarity	NPC279218
0.8993	High Similarity	NPC477957
0.8993	High Similarity	NPC473996
0.8986	High Similarity	NPC327059
0.8986	High Similarity	NPC321387
0.8986	High Similarity	NPC470908
0.8986	High Similarity	NPC472421
0.8958	High Similarity	NPC74397
0.8951	High Similarity	NPC137009
0.8951	High Similarity	NPC20709
0.8951	High Similarity	NPC471697
0.8951	High Similarity	NPC140890
0.8951	High Similarity	NPC225153
0.8951	High Similarity	NPC222342
0.8951	High Similarity	NPC265871
0.8951	High Similarity	NPC150648
0.8951	High Similarity	NPC329203
0.8951	High Similarity	NPC274784
0.8951	High Similarity	NPC310135
0.8944	High Similarity	NPC295261
0.8944	High Similarity	NPC287246
0.8944	High Similarity	NPC107586
0.8944	High Similarity	NPC32441
0.8944	High Similarity	NPC243083
0.8944	High Similarity	NPC12296
0.8944	High Similarity	NPC296490
0.8944	High Similarity	NPC79943
0.8944	High Similarity	NPC13768
0.894	High Similarity	NPC78554
0.894	High Similarity	NPC474609
0.894	High Similarity	NPC469936
0.894	High Similarity	NPC321372
0.894	High Similarity	NPC109967
0.894	High Similarity	NPC474738
0.894	High Similarity	NPC129053
0.894	High Similarity	NPC475797
0.8936	High Similarity	NPC60667
0.8929	High Similarity	NPC223457
0.8926	High Similarity	NPC471675
0.8926	High Similarity	NPC474744
0.8926	High Similarity	NPC474772
0.8926	High Similarity	NPC472423
0.8926	High Similarity	NPC295650
0.8921	High Similarity	NPC475589
0.8921	High Similarity	NPC473584
0.8921	High Similarity	NPC31872
0.8919	High Similarity	NPC277032
0.8919	High Similarity	NPC4423
0.8919	High Similarity	NPC77325
0.8904	High Similarity	NPC294365
0.8904	High Similarity	NPC171656
0.8897	High Similarity	NPC469542
0.8897	High Similarity	NPC73028
0.8897	High Similarity	NPC472344
0.8897	High Similarity	NPC276565
0.8897	High Similarity	NPC472006
0.8889	High Similarity	NPC188243
0.8889	High Similarity	NPC90411
0.8889	High Similarity	NPC307990
0.8889	High Similarity	NPC6407
0.8889	High Similarity	NPC182421
0.8889	High Similarity	NPC110228
0.8889	High Similarity	NPC16455
0.8881	High Similarity	NPC470671
0.8881	High Similarity	NPC329225
0.8881	High Similarity	NPC470399
0.8881	High Similarity	NPC470672
0.8881	High Similarity	NPC474487
0.8881	High Similarity	NPC147686
0.8881	High Similarity	NPC474504
0.8881	High Similarity	NPC131130
0.8881	High Similarity	NPC472460
0.8874	High Similarity	NPC199926
0.8873	High Similarity	NPC187826
0.8873	High Similarity	NPC470398
0.8873	High Similarity	NPC470397
0.8867	High Similarity	NPC271681
0.8867	High Similarity	NPC327269
0.8867	High Similarity	NPC285623
0.8867	High Similarity	NPC31627
0.8867	High Similarity	NPC476238
0.8865	High Similarity	NPC125920
0.8865	High Similarity	NPC236974
0.8865	High Similarity	NPC144027
0.8859	High Similarity	NPC267117
0.8859	High Similarity	NPC179178
0.8857	High Similarity	NPC25937
0.8857	High Similarity	NPC203817
0.8851	High Similarity	NPC10097
0.8849	High Similarity	NPC5515
0.8849	High Similarity	NPC270369
0.8844	High Similarity	NPC474302
0.8844	High Similarity	NPC260946
0.8836	High Similarity	NPC18886
0.8836	High Similarity	NPC113770
0.8836	High Similarity	NPC214166
0.8836	High Similarity	NPC478086
0.8836	High Similarity	NPC316816
0.8836	High Similarity	NPC255133
0.8836	High Similarity	NPC242100
0.8831	High Similarity	NPC92589
0.8828	High Similarity	NPC166689
0.8828	High Similarity	NPC312391
0.8828	High Similarity	NPC17170
0.8828	High Similarity	NPC156190
0.8828	High Similarity	NPC213322
0.8828	High Similarity	NPC4743
0.8828	High Similarity	NPC96408
0.8828	High Similarity	NPC279650
0.8828	High Similarity	NPC258630
0.8828	High Similarity	NPC150023
0.8828	High Similarity	NPC324386
0.8824	High Similarity	NPC470607
0.8819	High Similarity	NPC139554
0.8819	High Similarity	NPC316480
0.8819	High Similarity	NPC23257
0.8816	High Similarity	NPC150227
0.8811	High Similarity	NPC476480
0.8811	High Similarity	NPC84585
0.8808	High Similarity	NPC203080
0.8808	High Similarity	NPC469405
0.88	High Similarity	NPC472422
0.88	High Similarity	NPC471677
0.88	High Similarity	NPC215921
0.88	High Similarity	NPC70016
0.88	High Similarity	NPC471676
0.88	High Similarity	NPC474023
0.88	High Similarity	NPC471229
0.88	High Similarity	NPC244577
0.88	High Similarity	NPC263384
0.88	High Similarity	NPC240768
0.88	High Similarity	NPC290671
0.88	High Similarity	NPC200773
0.88	High Similarity	NPC472420
0.88	High Similarity	NPC474021
0.88	High Similarity	NPC190217
0.8794	High Similarity	NPC108113
0.8794	High Similarity	NPC93756
0.8792	High Similarity	NPC317492
0.8792	High Similarity	NPC164205
0.8792	High Similarity	NPC237440
0.8792	High Similarity	NPC472628
0.8792	High Similarity	NPC139966
0.8792	High Similarity	NPC307052
0.8792	High Similarity	NPC104236
0.8792	High Similarity	NPC270160
0.8784	High Similarity	NPC21835
0.8784	High Similarity	NPC3779
0.8784	High Similarity	NPC296998
0.8784	High Similarity	NPC23084
0.8784	High Similarity	NPC476182
0.8784	High Similarity	NPC473077
0.8784	High Similarity	NPC14875
0.8784	High Similarity	NPC176869
0.8784	High Similarity	NPC40086
0.8784	High Similarity	NPC44721
0.8784	High Similarity	NPC472627
0.8784	High Similarity	NPC472918
0.8784	High Similarity	NPC211466
0.8784	High Similarity	NPC122828
0.8776	High Similarity	NPC142731
0.8776	High Similarity	NPC472917
0.8776	High Similarity	NPC131568
0.8776	High Similarity	NPC306607
0.8776	High Similarity	NPC208176
0.8776	High Similarity	NPC311144
0.8776	High Similarity	NPC209040
0.8776	High Similarity	NPC184649
0.8776	High Similarity	NPC62290
0.8776	High Similarity	NPC470890
0.8776	High Similarity	NPC49130
0.8776	High Similarity	NPC4152
0.8776	High Similarity	NPC279417
0.8776	High Similarity	NPC326506
0.8776	High Similarity	NPC303185
0.8776	High Similarity	NPC131579
0.8768	High Similarity	NPC293453
0.8767	High Similarity	NPC220998
0.8767	High Similarity	NPC177354
0.8767	High Similarity	NPC112829

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC316535 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	851
0.2-0.3	1799
0.3-0.4	2468
0.4-0.5	2001
0.5-0.6	1135
0.6-0.7	444
0.7-0.8	149
0.8-0.85	36
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD1552	Clinical (unspecified phase)
0.8944	High Similarity	NPD1550	Clinical (unspecified phase)
0.8881	High Similarity	NPD1549	Phase 2
0.8758	High Similarity	NPD7075	Discontinued
0.8684	High Similarity	NPD7096	Clinical (unspecified phase)
0.8621	High Similarity	NPD970	Clinical (unspecified phase)
0.8618	High Similarity	NPD1934	Approved
0.8581	High Similarity	NPD6799	Approved
0.8542	High Similarity	NPD1510	Phase 2
0.8521	High Similarity	NPD1240	Approved
0.8516	High Similarity	NPD3749	Approved
0.8452	Intermediate Similarity	NPD3882	Suspended
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD2800	Approved
0.8435	Intermediate Similarity	NPD1243	Approved
0.8431	Intermediate Similarity	NPD7411	Suspended
0.8411	Intermediate Similarity	NPD920	Approved
0.8403	Intermediate Similarity	NPD1607	Approved
0.84	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD2532	Approved
0.84	Intermediate Similarity	NPD2534	Approved
0.84	Intermediate Similarity	NPD2533	Approved
0.8397	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD6801	Discontinued
0.8366	Intermediate Similarity	NPD4380	Phase 2
0.8366	Intermediate Similarity	NPD6599	Discontinued
0.8356	Intermediate Similarity	NPD2796	Approved
0.8356	Intermediate Similarity	NPD1551	Phase 2
0.8333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8278	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1511	Approved
0.821	Intermediate Similarity	NPD3818	Discontinued
0.8205	Intermediate Similarity	NPD2801	Approved
0.8158	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD3817	Phase 2
0.8133	Intermediate Similarity	NPD3750	Approved
0.8125	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD919	Approved
0.8105	Intermediate Similarity	NPD1512	Approved
0.8086	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6166	Phase 2
0.8086	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD5494	Approved
0.8052	Intermediate Similarity	NPD5403	Approved
0.8049	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD7768	Phase 2
0.7964	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD230	Phase 1
0.7947	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD9717	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7933	Intermediate Similarity	NPD2344	Approved
0.7925	Intermediate Similarity	NPD5402	Approved
0.7902	Intermediate Similarity	NPD1203	Approved
0.7901	Intermediate Similarity	NPD6959	Discontinued
0.7892	Intermediate Similarity	NPD7472	Approved
0.7872	Intermediate Similarity	NPD422	Phase 1
0.7862	Intermediate Similarity	NPD1465	Phase 2
0.7853	Intermediate Similarity	NPD5711	Approved
0.7853	Intermediate Similarity	NPD6232	Discontinued
0.7853	Intermediate Similarity	NPD5710	Approved
0.7844	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5953	Discontinued
0.7844	Intermediate Similarity	NPD6797	Phase 2
0.7838	Intermediate Similarity	NPD447	Suspended
0.7818	Intermediate Similarity	NPD7473	Discontinued
0.78	Intermediate Similarity	NPD2799	Discontinued
0.78	Intermediate Similarity	NPD3748	Approved
0.78	Intermediate Similarity	NPD7033	Discontinued
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD1247	Approved
0.7785	Intermediate Similarity	NPD6651	Approved
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7748	Intermediate Similarity	NPD2935	Discontinued
0.7727	Intermediate Similarity	NPD2309	Approved
0.7725	Intermediate Similarity	NPD7286	Phase 2
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7714	Intermediate Similarity	NPD9545	Approved
0.7651	Intermediate Similarity	NPD943	Approved
0.7635	Intermediate Similarity	NPD2313	Discontinued
0.7632	Intermediate Similarity	NPD6100	Approved
0.7632	Intermediate Similarity	NPD6099	Approved
0.7622	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.76	Intermediate Similarity	NPD5124	Phase 1
0.76	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2654	Approved
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3926	Phase 2
0.7571	Intermediate Similarity	NPD9493	Approved
0.7545	Intermediate Similarity	NPD2403	Approved
0.7544	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1296	Phase 2
0.7517	Intermediate Similarity	NPD3764	Approved
0.7517	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD3226	Approved
0.7486	Intermediate Similarity	NPD4287	Approved
0.7484	Intermediate Similarity	NPD1652	Phase 2
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7483	Intermediate Similarity	NPD1019	Discontinued
0.7483	Intermediate Similarity	NPD1933	Approved
0.7468	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7451	Intermediate Similarity	NPD4308	Phase 3
0.7451	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1608	Approved
0.7419	Intermediate Similarity	NPD2424	Discontinued
0.7417	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1613	Approved
0.7407	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3268	Approved
0.74	Intermediate Similarity	NPD6798	Discontinued
0.7383	Intermediate Similarity	NPD4908	Phase 1
0.7371	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7199	Phase 2
0.7362	Intermediate Similarity	NPD37	Approved
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7349	Intermediate Similarity	NPD6234	Discontinued
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4966	Approved
0.7315	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2797	Approved
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3887	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD5353	Approved
0.7267	Intermediate Similarity	NPD1729	Discontinued
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5647	Approved
0.7244	Intermediate Similarity	NPD6002	Phase 3
0.7244	Intermediate Similarity	NPD6005	Phase 3
0.7244	Intermediate Similarity	NPD6004	Phase 3
0.7244	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD17	Approved
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.723	Intermediate Similarity	NPD3225	Approved
0.7226	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1653	Approved
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7219	Intermediate Similarity	NPD6808	Phase 2
0.7216	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9269	Phase 2
0.72	Intermediate Similarity	NPD9494	Approved
0.72	Intermediate Similarity	NPD8313	Approved
0.72	Intermediate Similarity	NPD8312	Approved
0.719	Intermediate Similarity	NPD4307	Phase 2
0.7181	Intermediate Similarity	NPD3267	Approved
0.7181	Intermediate Similarity	NPD3266	Approved
0.7178	Intermediate Similarity	NPD7458	Discontinued
0.7172	Intermediate Similarity	NPD9268	Approved
0.7171	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2296	Approved
0.7169	Intermediate Similarity	NPD4288	Approved
0.7162	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7134	Intermediate Similarity	NPD2353	Approved
0.7133	Intermediate Similarity	NPD2798	Approved
0.7127	Intermediate Similarity	NPD4363	Phase 3
0.7127	Intermediate Similarity	NPD4360	Phase 2
0.7124	Intermediate Similarity	NPD6233	Phase 2
0.7123	Intermediate Similarity	NPD1778	Approved
0.7095	Intermediate Similarity	NPD1481	Phase 2
0.7088	Intermediate Similarity	NPD4361	Phase 2
0.7088	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6104	Discontinued
0.7074	Intermediate Similarity	NPD7584	Approved
0.7073	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1164	Approved
0.7063	Intermediate Similarity	NPD6190	Approved
0.7059	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7097	Phase 1
0.7027	Intermediate Similarity	NPD1091	Approved
0.7027	Intermediate Similarity	NPD1535	Discovery

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data